A4403

Sigma-Aldrich

L-Ascorbic acid

powder, suitable for cell culture, γ-irradiated

Synonym(s):
Antiscorbutic factor, Vitamin C, L-Threoascorbic acid
Empirical Formula (Hill Notation):
C6H8O6
CAS Number:
Molecular Weight:
176.12
Beilstein/REAXYS Number:
84272
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.75
Pricing and availability is not currently available.

Quality Level

biological source

synthetic (organic)

sterility

γ-irradiated

form

powder

mol wt

Mw 176.12 g/mol

application(s)

cell culture | insect: suitable
cell culture | mammalian: suitable
cell culture | plant: suitable

color

white to off-white

pH

1.0-2.5 (25 °C, 176 g/L in water)

mp

190-194 °C (dec.)

solubility

H2O: 10 mg/mL

SMILES string

OC([C@]([C@@H](O)CO)([H])O1)=C(O)C1=O

InChI

1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1

InChI key

CIWBSHSKHKDKBQ-JLAZNSOCSA-N

Gene Information

human ... SLC23A2(9962)

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General description

L-ascorbic acid is an unsaturated γ-lactone ring containing an enediol configuration (–COH=COH) attached with a carbonyl group.

Application

For use in cell culture applications as an antioxidant and to regenerate tocopherol.
L-ascorbic acid has been used:
  • in an osteogenic supplement for the growth of cells
  • as a component in the differentiation media
  • in WS-MSCs (Werner syndrome-mesenchymal stem cells) to study rescuing properties of ascorbic acid on aging defects

Biochem/physiol Actions

L-ascorbic acid mainly exhibits antioxidant properties. It protects plants from oxidative stress and mammals from diseases associated with oxidative stress. L-ascorbic acid mainly protects from hydroxyl radicals, superoxide and singlet oxygen. In addition, it also reduces the membrane-linked antioxidant α-tocopherol (oxidised form). L-Ascorbic acid enhances endothelium-dependent vasodilation in various disorders, including diabetes, coronary artery disease, hypertension and chronic heart failure.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

P L Conklin et al.
Plant physiology, 115(3), 1277-1285 (1997-12-09)
The biosynthesis of L-ascorbic acid (vitamin C) is not well understood in plants. The ozone-sensitive Arabidopsis thaliana mutant vitamin c-1 (vtc1; formerly known as soz1) is deficient in ascorbic acid, accumulating approximately 30% of wild-type levels. This deficiency could result...
Xi Wang et al.
Archives of oral biology, 57(9), 1231-1240 (2012-03-30)
This study focused on the characterization of stem cells from human exfoliated deciduous teeth (SHED) in comparison with dental pulp stem cells (DPSCs) to certify SHED as a key element in tissue engineering. In the present study, SHED and DPSCs...
R Heller et al.
The Journal of biological chemistry, 274(12), 8254-8260 (1999-03-13)
Ascorbic acid has been shown to enhance impaired endothelium-dependent vasodilation in patients with atherosclerosis by a mechanism that is thought to involve protection of nitric oxide (NO) from inactivation by free oxygen radicals. The present study in human endothelial cells...
Plant L-ascorbic acid: chemistry, function, metabolism, bioavailability and effects of processing.
Davey MW
Journal of the Science of Food and Agriculture, 80, 825-860 (2000)
Ying Li et al.
Protein & cell, 7(7), 478-488 (2016-06-09)
Werner syndrome (WS) is a premature aging disorder that mainly affects tissues derived from mesoderm. We have recently developed a novel human WS model using WRN-deficient human mesenchymal stem cells (MSCs). This model recapitulates many phenotypic features of WS. Based...
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